Ski-in/Ski-out holiday rentals in Western Massachusetts

We had a wonderful weekend at Liz’s cabin. Everything was clean. Hot tub was awesome. Would recommend to anyone looking for a beautiful cabin getaway.

The Pinnacle house was perfect for our families stay .. lots of room to spread out:) yet cozy & comfortable with a beautiful brand new kitchen ! Private & quiet & Mary Kay was so nice to reach out with easy instructions in & if anything needed be sure & let her know ! We hope to be back next year ! Everything you could possibly need there for your stay ! ! We loved it :)

The home is gorgeous - thoughtfully decorated, cozy and clean. The location is perfect for access to Stratton and to Manchester. The host, Jason, provided very clear and helpful instructions for check-in, check-out and use of the home and is friendly and attentive. This is a wonderful place to stay!

Very welcoming home, amenities were a great way to entertain ourselves during the night while kids were sleeping. The spacious living room, dining room and kitchen were an absolute dream! Would stay here again!

Tyler’s place exceeded expectations! The home was exactly as advertised—beautiful, spotless, and in a fantastic location. Check-in and check-out were seamless, making our stay even more enjoyable. Tyler was an outstanding host, incredibly responsive, and went above and beyond by providing detailed information and fantastic restaurant recommendations. I’d highly recommend staying here to anyone looking for a top-notch experience!

We had an amazing stay! David was quick to respond with any questions I had and even came out to hook up the propane tank for the heated pool. I saw in previous reviews about the tricky driveway but David’s description of it is perfectly accurate and not any trouble, just a little steep but nothing super tricky to deal with! The house has a beautiful setup and view, very clean and so much space. Even though it was cold and rainy we had the most fun and peaceful stay at this home. The bride of the bachelorette group said she wants to book with David on her own just for another stay/get-a-way! Highly recommend this beautiful space!

My husband and I spent a long last winter weekend here. The condo was perfect for ski on/off and we enjoyed a day on the mountain. Though the weather wasn’t great the whole time, Brittany & Jen were quick to send recommendations for things to do, trails to hike and their favorite restaurants. So close to lots of great spots in this little mountain town. We would absolutely stay here again

What an amazing experience! Our kids loved every second of it. Our hosts were amazing, responsive, and inviting. The home was beautiful and the scenery was spectacular. I highly recommend staying here. It was a great life experience! Thank you!

Nancy is a responsive host who provides clear instructions and offers local recommendations. The apartment we stayed in worked perfectly for our ski weekend at mount snow with 2 teens. Plenty of room and amenities within to foster a fun and relaxed family weekend. The maple syrup for purchase was a delicious touch. Would definitely stay again if we returned to the area.

The Sugar House was a fantastic place to stay! It was quiet and peaceful and there was a ton to explore in Burlington VT. The house had a lot of charm. it was cozy, warm, and had everything we needed for the weekend!

The unit is very comfortable for a family and very convenient to Mount Snow. Updated bathrooms and washer/dryer. Great clubhouse and pool facilities at Seasons condo. Andrew was a pleasure to work with.

We had a great time staying at Joann’s place! We came here with a group of friends from college and it was a perfect spot to hang out, play board games and a not far from some great hikes (would highly recommend Kaaterskill Falls Laurel House trail). The hot tub is great and the backyard is an awesome place to hang out. Joann was super communicative and responsive and went above and beyond to help with any issues as they arose. Would highly recommend her to anyone!

Great spot right next to Okemo! The cabin was better than the photos, felt really homey and clean.

We enjoyed our stay so much that I booked another night for the following weekend. The place is simple and beautiful. Secluded, surrounded by a pine forest, with a cozy meadow. The house has everything you need. While we were having dinner, a deer mama and her little Bambi were grazing right outside the windows. A wonderful experience in every way.

Terrance's place was clean, comfortable and quiet. Easy to find and the perfect stay. Terrance was very kind and hospitable.

Cozy spot with scenic views of Silver Lake. Our host Eric was responsive and provided detailed instructions on how to access the space and all of the perks included with the rental. Will definitely rebook if I ever find myself back in the area.

We had a wonderful cozy weekend with friends. Leopold’s place was private and tucked away with beautiful snowy Vermont scenery. We went skiing at Okemo (30 min drive) and then relaxed in the cozy living room. The shower was great and the bed was super comfortable. Thank you Leopold!

We had a wonderful time in this beautiful rural Vermont oasis. Exactly what we were looking for! The place is quintessential VT…. So if you are looking to spend a few nights in a reconverted barn on farmland…. Well, this is it. We loved being able to walk the property, and the jacuzzi and sauna were a real highlight. Directions getting in and figuring out our building were a bit confusing at first but we figured it out. We had a few small issues but Ben was responsive and did his best to take care of them quickly - with varying levels of success. The outdoor area could use some easier access and a bit more attention, but we were told that it is in the works. We would stay again in a heartbeat!

This was our second stay at Stone's Camp. It was just as great as the first stay. It's very private, peaceful and relaxing. We enjoyed hiking around the area and never had to leave the property in our car during our 4 night stay. The walk from the camp down the abandoned road to the washout is perfect. Our dogs enjoyed being off leash and exploring the woods and stream. It was especially nice for our 15 yro dog who is now unable to tackle larger hikes. Nights were spent enjoying a campfire by the babbling stream on rain free nights. Rainy nights were spent playing cards and games around the table indoors. If you are looking for something quiet, private and love to be outside and away from it all this is the place for you. If you have dogs it's the place for them as well. Thank you again, Chuck, for sharing your piece of paradise and thanks for accommodating our daughter and her boyfriend at the last minute who surprised us with a visit from the West Coast. We hope to be back!

One of my favorite Airbnb I’ve stayed so far. It was a perfect getaway, but also drivable distance from groceries stores. The amenities were amazing and the host Ben especially was super friendly, and their dog and their family as well. will definitely come back.

The Quimby Cabin was perfect! Very beautiful with the river right off the deck. We enjoyed a bonfire and ate every meal on the deck. There were lots of things for my kids to do, puzzles, games and drawing materials! I loved reading in the chairs on the deck. The kitchen was packed with everything I needed to cook some great meals too!

Cliff is very easy to communicate with. The house is in a great location, easy to find, and close to several ski resorts, making it very convenient for skiing. The room is comfortable and warm, and the kitchen is well-equipped, allowing you to cook your own meals. The game room, in particular, is a paradise for children, with countless games for you to enjoy. This was a wonderful experience, and I will definitely come back in the future.

As we ate breakfast looking out over the meadow and mountains, my partner spoke the truth: "This is the best Air B&B we've ever stayed at." You cannot imagine a more beautiful location, or a home more in keeping with its surroundings. We love an AirB&B with character -- this one has both character and soul. The kitchen is equipped for a chef; the living room is supremely comfortable; the bedrooms are comfy and spacious; everything you might need is within reach. But the true joy of the place is something much more than the sum of those parts. It's an inspiring spot, ideally situated for taking challenging bike rides, exploring swimming holes, and discovering the bakeries and farm stands of this beautiful hill country. Vivian was generous with her knowledge of the area and an extremely thoughtful host. We hope to come back!

This is a great little spot for a cozy, cabin getaway. Our family enjoyed our time there and all had enough space to be very comfortable. Also, a quiet location with a nature setting all around. Great deck to enjoy time outside. Close to local spots for food and seeing the town.